Solid-phase synthesis of an A-B loop mimetic of the C epsilon 3 domain of human IgE: macrocyclization by Sonogashira coupling

Spivey, A.C., McKendrick, J.E. ORCID: https://orcid.org/0000-0003-2275-0569, Srikaran, R. and Helm, B.A. (2003) Solid-phase synthesis of an A-B loop mimetic of the C epsilon 3 domain of human IgE: macrocyclization by Sonogashira coupling. Journal of Organic Chemistry, 68 (5). pp. 1843-1851. ISSN 0022-3263 doi: 10.1021/jo026693e

Abstract/Summary

The solid-phase synthesis of a cyclic peptide containing the 21-residue epitope found in the A-B loop of the Cepsilon3 domain of human immunoglobulin E has been carried out. The key macrocyclization step to form the 65-membered ring is achieved in similar to15% yield via an "on-resin" Sonogashira coupling reaction which concomitantly installs a diphenylacetylene amino acid conformational constraint within the loop.